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【结 构 式】 
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【药物名称】 【化学名称】N,N-Dimethyl-N-[2-[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethylperhydro-3,12-epoxypyrano[4,3-j]-1,2-benzodioxepin-10-yloxy]ethyl]amine oxalate 【CA登记号】139716-81-7 (non-specific stereoch.), 139716-80-6 (undefined isomer, free base) 【 分 子 式 】C21H35NO9 【 分 子 量 】445.5144 |
【开发单位】Academy of Military Medical Sciences (Originator), Shanghai Institute Materia Medica (Originator) 【药理作用】ANTIINFECTIVE THERAPY, Antimalarials, Treatment of Protozoal Diseases |
合成路线1
Dihydroartemisinin (II) was prepared by NaBH4 reduction of artemisinin (I). Condensation of (II) with 2-bromoethanol (A) in the presence of boron trifluoride etherate yielded the 10beta-bromoethyl acetal (III). Finally, reaction of (III) with dimethylamine in DMF provided the desired amine, which was finally converted to the oxalate salt.
| 【1】 Pan, J.-P.; Jiang, H.-J.; Wu, J.-M.; Zhu, Y.-M.; Wu, G.-S.; Li, Y.; Synthesis and antimalarial activity of artemisinin derivatives containing an amino group. J Med Chem 2000, 43, 9, 1635. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 15713 | Oxalic acid | 144-62-7 | C2H2O4 | 详情 | 详情 | |
| (A) | 10059 | Ethylene bromohydrin; 2-Bromo-1-ethanol | 540-51-2 | C2H5BrO | 详情 | 详情 |
| (I) | 22369 | Qinghaosu; Artemisine; (1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadecan-10-one | 63968-64-9 | C15H22O5 | 详情 | 详情 |
| (II) | 22370 | Dihydroartemisinin; (1R,4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadecan-10-ol | C15H24O5 | 详情 | 详情 | |
| (III) | 40705 | (1R,4S,5R,8S,9R,10S,12R,13R)-10-(2-bromoethoxy)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadecane; 2-bromoethyl (1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadec-10-yl ether | C17H27BrO5 | 详情 | 详情 |